EP0241281B1 - Substituted thiacycloalkeno [3,2-b] pyridines, methods of preparation, compositions and method of use - Google Patents

Substituted thiacycloalkeno [3,2-b] pyridines, methods of preparation, compositions and method of use Download PDF

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Publication number
EP0241281B1
EP0241281B1 EP87303064A EP87303064A EP0241281B1 EP 0241281 B1 EP0241281 B1 EP 0241281B1 EP 87303064 A EP87303064 A EP 87303064A EP 87303064 A EP87303064 A EP 87303064A EP 0241281 B1 EP0241281 B1 EP 0241281B1
Authority
EP
European Patent Office
Prior art keywords
compound
methyl
pyridine
carboxylate
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP87303064A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0241281A3 (en
EP0241281A2 (en
Inventor
Charles F. Schwender
John H. Dodd
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ortho Pharmaceutical Corp
Original Assignee
Ortho Pharmaceutical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US06/849,647 external-priority patent/US4705785A/en
Application filed by Ortho Pharmaceutical Corp filed Critical Ortho Pharmaceutical Corp
Publication of EP0241281A2 publication Critical patent/EP0241281A2/en
Publication of EP0241281A3 publication Critical patent/EP0241281A3/en
Application granted granted Critical
Publication of EP0241281B1 publication Critical patent/EP0241281B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis

Definitions

  • novel compounds of the present invention may be synthesized according to the following reaction scheme wherein R1, R2, R3, R4, R5, are as defined above, MCPBA signifies m-chloroperoxybenzoic acid, and Y is p-methylphenyl or alkyl.
  • MCPBA signifies m-chloroperoxybenzoic acid
  • Y is p-methylphenyl or alkyl.
  • Compounds of the formula I, wherein n is 1-12 may be prepared by stirring equal molar amounts of for example 3-oxotetrahydrothiophene-1,1-dioxide, the appropriately substituted aldehyde of formula VII and the substituted 3-aminoester of formula VI in ethanol for two to twenty-four hours at room temperature (see example 4).
  • the resultant hydroxy intermediate of formula VIII is a novel compound. Said compound VIII is then heated in refluxing toluene for one to twenty-four hours to effect dehydration, thus producing compound Ia (see example 5).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Obesity (AREA)
  • Diabetes (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Hematology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Endocrinology (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Manufacturing Of Magnetic Record Carriers (AREA)
  • Catalysts (AREA)
EP87303064A 1986-04-09 1987-04-08 Substituted thiacycloalkeno [3,2-b] pyridines, methods of preparation, compositions and method of use Expired - Lifetime EP0241281B1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US06/849,647 US4705785A (en) 1986-04-09 1986-04-09 Substituted thiacycloalkeno (3,2-b) pyridines and pharmaceutical compositions and method of use
US07/010,858 US4777167A (en) 1986-04-09 1987-02-04 Pharmaceutically useful substituted thiacycloalkeno [3,2-b]pyridines, compositions and method of use
US849647 1987-02-17
US10858 1998-01-22

Publications (3)

Publication Number Publication Date
EP0241281A2 EP0241281A2 (en) 1987-10-14
EP0241281A3 EP0241281A3 (en) 1989-01-25
EP0241281B1 true EP0241281B1 (en) 1994-07-27

Family

ID=26681670

Family Applications (1)

Application Number Title Priority Date Filing Date
EP87303064A Expired - Lifetime EP0241281B1 (en) 1986-04-09 1987-04-08 Substituted thiacycloalkeno [3,2-b] pyridines, methods of preparation, compositions and method of use

Country Status (20)

Country Link
US (1) US4777167A (da)
EP (1) EP0241281B1 (da)
JP (2) JP2613758B2 (da)
KR (1) KR950014868B1 (da)
CN (2) CN1028759C (da)
AT (1) ATE109151T1 (da)
CA (1) CA1310967C (da)
DE (1) DE3750271T2 (da)
DK (2) DK167021B1 (da)
ES (1) ES2060597T3 (da)
FI (1) FI93454C (da)
HK (1) HK32395A (da)
HU (1) HU199480B (da)
IE (1) IE63854B1 (da)
IL (1) IL82145A0 (da)
MY (1) MY100499A (da)
NO (1) NO169072C (da)
NZ (1) NZ219761A (da)
PH (1) PH26673A (da)
PT (1) PT84648B (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0308371A1 (de) * 1987-09-18 1989-03-22 Ciba-Geigy Ag 4-Azasaccharine, 4-Aza-dihydro-oder-tetrahydrosaccharine und Verfahren zu deren Herstellung
IT1265647B1 (it) * 1992-11-18 1996-11-22 Farmin Srl Composizione farmaceutiche topiche per le allergie respiratorie
DE4424678A1 (de) * 1994-07-13 1996-01-18 Bayer Ag Dioxo-thiopyrano-pyridin-carbonsäure-derivate
US6265417B1 (en) 1997-12-18 2001-07-24 Abbott Laboratories Potassium channel openers
US6593335B1 (en) 1997-12-18 2003-07-15 Abbott Laboratories Potassium channel openers
ES2222000T3 (es) * 1997-12-18 2005-01-16 Abbott Laboratories Compuestos que abren los canales de potasio.
IL147540A0 (en) 1999-07-12 2002-08-14 Ortho Mcneil Pharm Inc OXATHIEPINO [6,5-b] DIHYDROPYRIDINES, AND RELATED COMPOSITIONS AND METHODS
AU7102700A (en) * 1999-09-22 2001-04-24 Ortho-Mcneil Pharmaceutical, Inc. Benzo-fused dithiepino[6,5-b]pyridines, and related compositions and methods

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2616995A1 (de) * 1976-04-17 1977-10-27 Bayer Ag 1.4-dihydropyridine mit schwefelhaltigen substituenten mehrere verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
US4285955A (en) * 1978-10-31 1981-08-25 Bayer Aktiengesellschaft 1,4-Dihydropyridinecarboxylic acids
NZ201395A (en) * 1981-07-30 1987-02-20 Bayer Ag Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines
JPS6210087A (ja) * 1985-07-03 1987-01-19 Shionogi & Co Ltd ４，７−ジヒドロチエノ〔２，３−ｂ〕ピリジン誘導体，その製造法および循環器系疾患治療剤

Also Published As

Publication number Publication date
CN1028759C (zh) 1995-06-07
HK32395A (en) 1995-03-17
IE870913L (en) 1987-10-09
JP2613758B2 (ja) 1997-05-28
DK180487D0 (da) 1987-04-08
ATE109151T1 (de) 1994-08-15
DE3750271T2 (de) 1994-11-24
JP2613757B2 (ja) 1997-05-28
KR870010057A (ko) 1987-11-30
NO169072B (no) 1992-01-27
JPH08208660A (ja) 1996-08-13
PH26673A (en) 1992-09-13
DK147392A (da) 1992-12-08
CN1067076C (zh) 2001-06-13
DK167021C (da) 1993-08-16
FI93454C (fi) 1995-04-10
CN87102761A (zh) 1987-11-04
IL82145A0 (en) 1987-10-30
DK147392D0 (da) 1992-12-08
PT84648B (pt) 1989-12-29
HUT47117A (en) 1989-01-30
NZ219761A (en) 1989-02-24
CA1310967C (en) 1992-12-01
ES2060597T3 (es) 1994-12-01
MY100499A (en) 1990-10-30
DE3750271D1 (de) 1994-09-01
NO169072C (no) 1992-05-06
EP0241281A3 (en) 1989-01-25
DK180487A (da) 1987-10-10
FI871535A (fi) 1987-10-10
US4777167A (en) 1988-10-11
FI93454B (fi) 1994-12-30
KR950014868B1 (ko) 1995-12-16
DK169762B1 (da) 1995-02-20
DK167021B1 (da) 1993-08-16
HU199480B (en) 1990-02-28
NO871481D0 (no) 1987-04-08
PT84648A (en) 1987-05-01
CN1102185A (zh) 1995-05-03
EP0241281A2 (en) 1987-10-14
IE63854B1 (en) 1995-06-14
NO871481L (no) 1987-10-12
JPH08208659A (ja) 1996-08-13
FI871535A0 (fi) 1987-04-08

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